Strapless Casual Maxi Dresses
Strapless casual maxi dresses are the ultimate power move for those days when you want to look effortlessly put-together without even trying. Whether you’re headed out with your crew or just vibing solo, these easy-breezy silhouettes have your back—no straps, no problem. Slip into a strapless casual maxi dress and watch how quickly you become the main character, turning every sidewalk into your runway. Because sometimes, the best kind of drama is in your outfit, not your group chat.
$42.90
A strapless black floral mesh maxi dress with a bodycon fit and high-side slit.
$39.90
A strapless black mesh maxi dress featuring a floral print, high side slit, and form-hugging silhouette.
$44.90
A strapless burgundy mesh maxi dress featuring a bold floral print and a dramatic high side slit.
$42.90
A strapless taupe maxi dress in stretchy knit fabric featuring a vibrant floral print and side slit.
$42.90
A chartreuse ribbed knit midi dress featuring a strapless sweetheart neckline, keyhole cutout, and high slit.
$34.90
A chic strapless brown maxi dress with a high slit and flattering bodycon silhouette.
$39.90
A strapless tropical palm print maxi dress with a high side slit and form-hugging silhouette.
$59.90
A strapless red brown knit maxi dress featuring a cutout bodice, metal accent, and high front slit.
$59.90
An ivory A-line maxi dress with gauze fabric, sheer lace insets, and a faux leather belt.
$42.90
A black tropical print strapless maxi dress in stretchy knit fabric with a side cutout and high slit.
$42.90
A coral strapless maxi dress featuring sheer floral mesh, ruched bust, and a thigh-high side slit.
$46.90
A natural knit crochet maxi dress featuring a strapless twist neckline and curve-hugging silhouette.
$39.90
A strapless natural floral maxi dress featuring a flirty cutout, mesh-lined fabric, and form-hugging silhouette.
$46.90
A bold ivory maxi tube dress in lightweight woven fabric, featuring a geometric print and fringe trim.
$56.90
A strapless natural woven maxi dress featuring a tropical print, belted waist, side slit, and pockets.
$34.90
A light blue floral mesh maxi dress featuring a strapless neckline and curve-hugging, elegant silhouette.
$39.90
An orange abstract print maxi dress featuring a strapless tube neckline, stretchy knit fabric, and high side slit.
$42.90
A strapless black knit maxi dress featuring a pleated waist and curve-hugging, slinky silhouette.
$59.90
A dreamy white floral maxi dress with an open tie back and ruffled silhouette.
$44.90
A black floral maxi dress featuring sheer mesh, a lace-up strappy back, and a form-hugging silhouette.
$32.90
A sleeveless black knit maxi dress featuring a crew neckline, bodycon silhouette, and flirty side slit.
$29.97 $79.90 62% off
An elegant strapless satin dress in orange featuring a high ruffled slit and curve-hugging silhouette.
$35.90
A black knit maxi dress featuring a front keyhole cutout and a curve-hugging, textured silhouette.
$35.90
A strapless white floral midi dress with a form-hugging fit and chic flared hem.
$49.90
An ivory strapless floral skater dress with a ruffled hem, perfect for casual outings.
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Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: XS | Rhinestone
Sultry and stunning, the Alisha formal dress will keep all eyes on you. With thin rhinestone detailed straps that give effortless sparkle and a curve-hugging silhouette, and an alluring high slit. Fit & FeaturesLightweight, breathable stretchy fabric, Sleeveless cowl neckline, Rhinestone detailed straps, High waist seam, Floor-length hem, form-fitting silhouette, high slit, Runs true to size, Where to Wear:Prom, glamorous evenings, dinner parties, weddings Free Shipping on All Orders Over $75. | Windsor Alisha Rhinestone Strap Formal Dress in Black | Size: M | Stretchy Fabric/Rhinestone
Enchant the room instantly in this gorgeous floor-length gown! Ella features a stunning sleeveless cowl neck, flattering high slit, and sleek spaghetti straps. Fit & FeaturesStretch satin lined fabric, Cowl neck, sleek spaghetti straps, Form-fitting silhouette, high-side slit, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, fancy date nights, cocktail parties, engagement parties, rehearsal dinners Free Shipping on All Orders Over $75. | Windsor Ella Cowl Neck Satin Dress in Mauve-2 | Size: S | Satin Fabric
A floral print adds to the dreamy charm of this flowy maxi dress boasting an open tie back design and ruffled silhouette perfect for beachside strolls or day parties. Fit & FeaturesFloral print, woven fabric, short woven lining, Sweetheart neckline with bust tie, Spaghetti straps, Open tie back design, Ruffled flowy silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Sunshine Dream Open Tie Back Floral Maxi Dress in White | Size: M | Woven Fabric
Perfect for your vacay in Tulum, this one-shoulder tropical maxi dress was made for sunset dinners and dancing! Fit & FeaturesTropical print, smooth knit fabric with short stretchy lining, One-shoulder neckline, One shoulder strap with metal accents, Front ruffled slit, Bodycon silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor In Tulum One-Shoulder Tropical Maxi Dress in Black | Size: M | Knit Fabric
Evoke chic romance on date night in this gorgeous floral maxi dress designed with an open lace-up strappy back and floor-length form-hugging silhouette. Style with a sleek handbag and stiletto heels. Fit & FeaturesSheer mesh fabric with knit lining, high stretch, Large floral print, Sleeveless deep V-neckline, Spaghetti straps, Open cross-back lace-up strappy design, Maxi-length hem, form-hugging silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Chic Romance Floral Lace-Up Maxi Dress in Black | Size: L | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Achieve a glowing radiance in this metallic knit maxi dress for vacation or sunset cocktails! Featuring a seductive plunge cowl halter neckline and a form-hugging silhouette, this dress accentuates your curves with effortless elegance while the back slit offers easy movement. Fit & FeaturesMetallic knit fabric, knit lining, moderate stretch, Plunge cowl halter neckline, Adjustable strappy open back, Form-hugging silhouette, Back slit, maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Glow Goddess Strappy Back Metallic Knit Maxi Dress in Gold | Size: XS | Knit Fabric
Your new laid-back fave tank maxi dress for styling up or down for any occasion! Crafted from rib knit fabric, this crew neck dress offers a form-hugging fit and a maxi-length hem for a flattering silhouette. Complete the look in cute sandals and sunnies! Fit & FeaturesRib-knit stretchy fabric, Crew neck, Form-hugging maxi silhouette, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Laid Back Fave Crew Neck Tank Maxi Dress in Black | Size: M | Knit Fabric/Stretchy Fabric
Enjoy a sunset dinner and drinks in this floral maxi dress along the Amalfi Coast! With sultry details and a mermaid silhouette that flaunts your curves, this dress will turn heads. Fit & FeaturesFloral print, mesh fabric lined with stretchy knit, Plunge halter cowl neckline, tie closure, Mermaid silhouette, Maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Amalfi Coast Plunge Neck Mermaid Floral Maxi Dress in Burgundy | Size: S | Mesh Fabric/Mesh Fabric
Perfect for any occasion, this floral maxi dress will make a statement! The strapless neckline and maxi hem create a flattering silhouette, while the vibrant floral print and side slit add a touch of playful elegance. Fit & FeaturesFloral print, mesh fabric, soft knit stretchy lining, Strapless neckline, Side slit, Form-hugging fit, Relaxed maxi-length hem, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Statement Blooms Strapless Floral Maxi Dress in Taupe | Size: L | Knit Fabric/Mesh Fabric/Mesh Fabric
Strapless Casual Maxi Dresses
When it comes to looking effortlessly put-together with zero stress, strapless casual maxi dresses are the ultimate go-to for our girls who want to keep it cute and comfy all day long. Picture this: you’re running out the door for brunch with your besties, iced coffee in hand, and you just throw on a strapless maxi—suddenly, you’re serving main character energy without even trying. These dresses are your ride-or-die for everything from spontaneous road trips to rooftop hangs, backyard BBQs, or just living your best life in the sunshine. The beauty of a strapless maxi is in its versatility; it’s the dress you reach for when you want to show off those shoulders and soak up every golden hour moment, but still keep things breezy and easy. Whether you’re petite, tall, curvy, or somewhere in between, there’s a strapless maxi out there ready to hype you up and make you feel like the goddess you are. And let’s be real: they’re a total lifesaver when you want to skip the fuss of straps and complicated fastenings—just slip it on, add a pair of sandals or your favorite sneakers, and you’re out the door in seconds flat.
Gifting a strapless casual maxi dress? You’re basically guaranteeing yourself a spot in the BFF hall of fame. These dresses are the ultimate present for birthdays, graduations, or just because your bestie deserves a little extra sparkle in her wardrobe. They’re a dreamy pick for anyone who loves to keep it chill but still wants to turn heads—think sisters, cousins, roommates, or even that friend who swears she “has nothing to wear.” And if you’re shopping for yourself (because self-love is the best kind, hello), you’ll want to keep a few things in mind: look for soft, breathable fabrics that feel like a hug, and pay attention to little details like smocked bodices, flowy skirts, or cute side slits that let you move like you own the place. Don’t sleep on pockets, either—they’re a total game-changer for stashing lip gloss, your phone, or a snack for later (priorities, right?). Styling a strapless maxi is all about playing with layers and accessories. Toss on a denim jacket when the breeze picks up, or stack up the bangles and go bold with your favorite sunnies for that carefree, festival-ready vibe. And if you want to keep your look fresh all season long, check out our Casual Summer Maxi Dresses collection for more inspo and endless outfit possibilities.
Living in strapless casual maxi dresses is basically a cheat code for feeling flirty and free, no matter what’s on your calendar. These dresses are made for twirling barefoot in the grass, catching sunsets with your crew, or dancing the night away under string lights. They’re the perfect canvas for showing off your favorite statement earrings or that tan you worked so hard for, and they transition seamlessly from lazy afternoons to spontaneous nights out. If you’re all about maximizing comfort without sacrificing style, this is your sign to stock up and let your wardrobe do the heavy lifting. After all, every Windsor girl deserves to feel unstoppable, and nothing says “I’ve got this” quite like the easy, breezy confidence of a strapless maxi dress.